Use of phenylacetamides as plant protectives having herbicidal and fungicidal effect

ABSTRACT

The resent invention relates to the use of phenylacetamides as crop protection agents, to novel crop protection compositions comprising, as active compounds, phenylacetamides, and to novel phenylacetamides. 
     The present invention provides the use of phenylacetamides of the formula I                    
     as crop protection agents having herbicidal and/or fungicidal action, where the radicals have the following meanings: 
     A is an unsubstituted or substituted aryl radical; 
     R 1  is an unsubstituted or substituted aryl radical; 
     R 2 , R 3  are hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylaryl, which may be unsubstituted or partially or fully halogenated or may carry one to three substituents selected from the group consisting of C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 3 -C 7 -cycloalkyl, C 5 -C 7 -cycloalkenyl; 
     R 4  is hydrogen or C 1 -C 6 -alkyl; 
     R 5  is hydroxyl, C 1 -C 4 -alkoxy, aryl-C 1 -C 4 -alkoxy, aryloxy, 
     and their agriculturally useful salts.

This application is a 371 of PCT/EP00/01409 filed Feb. 21, 1999.

The present invention relates to the use of phenylacetamides as cropprotection agents, to novel crop protection compositions comprising, asactive compounds, phenylacetamides, and to novel phenylacetamides.

The present invention provides the use of phenylacetamides of theformula I

as crop protection agents, where the radicals have the followingmeanings:

A is aryl which can be mono- or polysubstituted by the following groups:hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato,carboxyl, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-cyanoalkyl, C₂-C₆-alkyenyl, C₁-C₆-alkoxy-C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₃-C₆-alkynyl-C₁-C₆-alkoxy,C₃-C₇-cycloalkyl, C₁-C₆-alkyl-C₃-C₇-cycloalkyl,C₁-C₆-alkoxy-C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy,C₃-C₇-cyanocycloalkoxy, C₁-C₆-alkyl-C₃-C₇-cycloalkoxy,C₃-C₇-halocycloalkyl, C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy,C₅-C₇-cycloalkenyl, C₁-C₆-alkyl-C₅-C₇-cycloalkenyl,C₁-C₆-alkoxy-₅-C₇-cycloalkenyl, C₅-C₇-cyanocycloalkenyl,C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl, C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy,C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy,C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy,C₁-C₆-alkylthio, C₁-C₆-cyanoalkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkylcarboxyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl,C₁-C₆-alkylcarbonylamino, arylcarbonylamino, arylsulfinyl, arylsulfonyl,heteroarylsulfinyl, heteroarylsulfonyl, aryl-C₁-C₆-alkyl,aryl-C₂-C₆-alkenyl, aryl-C₃-C₆-alkynyl, aryl-C₁-C₆-alkoxy,aryl-C₂-C₆-alkenyloky, aryl-C₃-C₆-alkynyloxy, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, aryl,aryloxy, arylthio or —C(R⁴)═NR⁵,

R¹ is aryl or aryl-C₁-C₆-alkyl, where the aryl radical can in each casebe mono- or polysubstituted by the following groups: hydrogen, halogen,cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino,C₁-C₆-alkyl, C₁-C₆-alkoxy- C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl,C₁-C₆-alkoxy- C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁C₆-alkoxy- C₃-C₆-alkynyl,C₃-C₆-alkynyl-C₁C₆-alkoxy, C₃-C₇-cycloalkyl,C₁-C₆-alkyl-C₃-C₇-cycloalkyl, C₁-C₆-alkoxy- C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyloxy, C₃-C₇-cyanocycloalkoxy,C₁-C₆-alkyl-C₃-C₇-cycloalkoxy, C₃-C₇-halocycloalkyl,C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy, C₅-C₇-cycloalkenyl,C₁-C₆-alkyl- C₅-C₇-cycloalkenyl, C₁-C₆-alkoxy- C₅-C₇-cycloalkenyl,C₅-C₇-cyanocycloalkenyl, C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂_(C) ₆-haloalkenyl, C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl,C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy, C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy,C₂-C₆-alkenyloxy, C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy,C₂-C₆-alkynyloxy, C_(-C) ₆-alkylthio, C₁-C₆-cyanoalkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarboxyl- C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl- C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino,arylcarbonylamino, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl,heteroarylsulfonyl, aryl-C₁-C₆-alkyl, aryl-C₂-C₆-alkenyl,aryl-C₃-C₆-alkynyl, aryl-C₁-C₆-alkoxy, aryl-C₂-C₆-alkenyloxy,aryl-C₃-C₆-alkynyloxy, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, aryl, aryloxy, arylthio or—C(R⁴)═NR⁵,

R², R³ are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl,C₁-C₆-alkylaryl, which may be unsubstituted or partially or fullyhalogenated or may carry one to three substituents selected from thegroup consisting of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁C₄-alkylthio,C₃-C₇-cycloalkyl, C₅-C₇-cycloalkenyl;

R⁴ is hydrogen or C₁-C₆-alkyl,

R⁵ is hydroxyl, C₁-C₄-alkoxy, aryl- C₁-C₄-alkoxy, aryloxy,

and their agriculturally useful salts.

Some of the compounds of the formula I are known from the literature.

WO 95/35283 describes trisubstituted phenyl derivatives as medicamentswhich act as PDE IV (phosphodiesterase IV) inhibitors. It describes inparticular compounds of the following formula

where W is, inter alia, the group ═C(Y)—, where Y=halogen, alkyl,—X—R^(a) or —N(R^(b)), where X=O, S, SO, SO₂; R^(a)=hydrogen, alkyl;R^(b)=hydrogen or alkyl; L=—CH(R¹) (R²) where R¹ and R²=CN or —CONR⁹R¹⁰and R⁹ and R¹⁰=hydrogen, alkyl, aralkyl or aryl; Z=one of the groups(A)-(D), described in more detail therein, where these groups have to besubstituted by at least one aryl group (Ar).

EP 0 466 640 describes alpha-carbonylphenylacetonitrile derivatives asstabilizers for organic materials. The compounds of the formula

which are disclosed in that publication are suitable for stabilizinglubricating oils, fluids for processing metals, hydraulic fluids andthermoplastic polymers and elastomers. In the formula shown above, A is,inter alia, the group —NR⁶R⁷, where R⁶, R⁷ may, inter alia, be hydrogenand unsubstituted phenyl or naphthyl. Two radicals R, R¹, R², R³ or R⁴which are attached ortho to one another may also form the group—CH═CH—CH═CH—(naphthyl group).

DD 156,663 describes compounds of the formula below for use as plantgrowth stimulating agents for use in crop plants, such as, for example,maize, sunflower, tomato, soybean or beans:

The radicals have, inter alia, the following meanings: R₁, R₂: hydrogen,alkyl, cycloalkyl, aryl, haloaryl, aralkyl, alkenyl or alkanoyl; R₃:hydrogen or alkyl. The compounds described are characterized by the factthat the phenyl group is in each case unsubstituted.

DE 2 008 692 describes cyanophenylacetamide derivatives of the formulabelow

as starting materials or intermediates for preparing indole-3-carboxylicacid derivatives. R₁ and R₂ are hydrogen, alkyl or aralkyl. The tworadicals X and Y on the phenyl ring are, inter alia, hydrogen, halogen,alkyl, alkoxy, aralkoxy, trifluoromethyl, hydroxyl, amino, nitro,carboxyl or sulfoxy. Additionally, the phenyl ring may be substituted byan amino or nitro group.

Furthermore, the following individual compounds of the formula I areknown from the scientific literature:

a) The compound where A=phenyl, R¹=4-ethoxyphenyl, R²=H, R³=n-C₄H₉[N-(4-ethoxyphenyl)-2-cyano-2-phenylhexanamide] from Arch. Pharm. 321(1988): 107.

b) The compound where A=phenyl, R¹=4-ethoxyphenyl, R²=H, R³=C₂H₅;[N-(4-ethoxyphenyl)-2-cyano-2-phenylbutanamide from Arch. Pharm. 321(1988), 739.

c) The compound where A=phenyl, R¹=2,4,6-trimethoxyphenyl, R²=H, R³=H;[N-(2,4,6-trimethoxyphenyl)-2-cyano-2-phenylacetamide] from J. Med.Chem. 39,20 (1996), 3908.

d) The compound where A=4-methoxyphenyl, R¹=2,6-dimethylphenyl, R²=H,R³=H; [N-(2,6,-dimethylphenyl)-2-cyano-2-phenylacetamide] from LiebigsAnn. Chem. 3, (1992): 239.

e) The compounds where A=phenyl, R¹=2-methylphenyl, 3-methylphenyl or4-methylphenyl, R²=H, R³=H;[N-(2-methylphenyl)-2-cyano-2-phenylacetamide;N-(3-methylphenyl)-2-cyano-2-phenylacetamide;N-(4-methylphenyl)-2-cyano-2-phenylacetamide] from Am. Chem. J. 39(1908), 76.

Surprisingly, it has been found that compounds of the formula I can beused as crop protection agents having fungicidal and/or herbicidalaction. They are suitable for treating plants, for example forcontrolling harmful fungi in useful plants (fungicidal action) or forcontrolling undesirable plant growth in the case of harmful plants(herbicidal action).

Compounds of the formula I can be prepared analogously to the processesknown from the literature (for example J. Am. Chem. Soc. 39 (1908), 63;DD 156663). The starting materials are either known from the literatureor they can be prepared analogously to methods known from theliterature, or they are commercially available.

The present invention furthermore provides crop protection compositionswhich comprise the compounds of the formula I, with the exception of thecompounds described in DD 156,663 as plant-growth-regulating agents.What is meant in this context are in particular crop protectioncompositions which comprise the compounds I, with the proviso that

a) if A is an unsubstituted phenyl group and R³ is hydrogen or alkyl, R¹is not unsubstituted phenyl or halogen-substituted phenyl;

b) if R³ is hydrogen, A is not 2-nitrophenyl or 2-aminophenyl.

The present invention furthermore provides novel compounds of theformula I as described above, except for the compounds described in WO95/35283, EP 0 466 640, DD 156663 and DE 2008692 and the individualcompounds mentioned above under a)-e). What is meant in this context arein particular those compounds of the formula I, with the proviso that

a) if A is an unsubstituted phenyl group and R³ is hydrogen or alkyl, R¹is not unsubstituted phenyl or halogen-substituted phenyl;

b) if R³ is hydrogen, A is not 2-nitrophenyl or 2-aminophenyl;

c) if R³ is hydrogen, R¹ is hydrogen, alkyl or alkylaryl, A is notphenyl which is substituted directly or indirectly by an aryl group.

In the definition of the different radicals in the formula I, the giventerms, either on their own (such as, for example, C₁-C₆-“alkyl”) or asparts of or in combination with other composite chemical groups (suchas, for example, C₁-C₆-halo-“alkyl”, alkoxy-C₁-C₆-“alkyl”), are inprinciple collective terms for a group of compounds. If theabovementioned groups can be mono- or polysubstituted, the substituentscan in principle be identical or different.

Halogen is in each case fluorine, bromine, chlorine or iodine, inparticular fluorine or chlorine.

Examples of other meanings are:

C₁-C₄-alkyl and all alkyl moieties of correspondingly composed chemicalgroups, such as, for example, alkylamino, dialkylamino, alkylaryl,cyanoalkyl, haloalkyl, etc.: a straight-chain or branched alkyl radical,such as, for example, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, in particularmethyl or ethyl;

C₁-C₆-alkyl: a straight-chain or branched C₁-C₆-alkyl radical, such as,for example, C₁-C₄-alkyl as mentioned above, and also pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-3-methylpropyl;

C₂-C₆-alkenyl and all alkenyl moieties of correspondingly composedgroups, such as, for example, alkenyloxy, haloalkenyl, haloalkenyloxy,etc.: a straight-chain or branched alkenyl radical, such as, forexample, ethylene, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl and2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl,penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl,3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl,hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl,4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl,2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl,4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl,1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl,1,2-dimetylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,1,3-dimetylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl,1,3-dimetylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl,2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl,2,3-dimetylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-2-en-1-yl,2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl,1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and1-ethyl-2-methylprop-2-en-1-yl;

C₂-C₆-alkynyl, and all alkynyl moieties of correspondingly composedchemical groups, such as, for example, alkynyloxy or alkynylalkoxy,etc.: for example ethynyl, propargyl, but-1-yn-3-yl, but-1-yn-4-yl,but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl,pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl,hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl,hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-ylor 4-methylpent-2-yn-5-yl;

C₁-C₆-haloalkyl is a C₁-C₆-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, for example trichloromethyl, trifluoromethyl, 2-fluoroethyl,2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2,2,2-trichloroethyl, 2-fluoropropyl, 3-fluoropropyl, 2-chloropropyl or3-chloropropyl, in particular 2-fluoroethyl or 2-chloroethyl;

C₁-C₆-alkoxy and all alkoxy moieties of correspondingly composedchemical groups, such as, for example, alkoxyalkyl, alkoxyalkenyl,alkoxyalkynyl, alkoxycarbonyl, etc.: a straight-chain or branched alkoxyradical, such as, for example, methoxy, ethoxy, propoxy, 1-methylethoxy,butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, inparticular methoxy or ethoxy;

halo-C₁-C₆-alkoxy is a C₁-C₆-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine or bromine;

halo-C₂-C₆-alkenyl is a C₂-C₆-alkenyl radical as mentioned above whichis partially or fully substituted by fluorine, chlorine or bromine;

halo-C₂-C₆-alkynyl is a C₂-C₆-alkynyl radical as mentioned above whichis partially or fully substituted by fluorine, chlorine or bromine;

C₃-C₈-cycloalkyl and all cycloalkyl moieties of correspondingly composedchemical groups, such as, for example, cycloalkylalkoxy,alkylcycloalkyl, alkylcycloalkyloxy, cycloalkyloxy, etc.: cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl;

C₃-C₈-cycloalkenyl and all cycloalkenyl moieties of correspondinglycomposed chemical groups, such as, for example, alkylcycloalkenyl,cyanocycloalkenyl, etc.: cyclopropenyl, cyclobutenyl, cyclopentenyl,cyclohexenyl, cycloheptenyl, cyclooctenyl; C₁-C₆-alkyl-carbonyl and allalkylcarbonyl moieties of correspondingly composed chemical groups, suchas, for example, alkylcarbonylalkyl, alkylcarbonylamino, etc.: acarbonyl group which is substituted by a C₁-C₆-alkyl radical such as,for example, methylcarbonyl, ethylcarbonyl, propylcarbonyl,1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl,2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;

C₁-C₆-alkylthio is a sulfur atom which is substituted by a C₁-C₆-alkylradical as mentioned above;

C₁-C₆-cyanoalkyl: for example cyanomethyl, 1-cyanoeth-1-yl,2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl,1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl,3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl,1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl or2-cyanomethylprop-2-yl;

aryl and all aryl moieties of correspondingly composed chemical groups,such as, for example, aryl-C₁-C₆-alkyl, aryl-C₂-C₆-alkenyl, aryloxy,arylthio, arylcarbonylamino, etc.: a mono-to tricyclic aromatic ringsystem containing 6-14 carbon ring members, such as, for example,phenyl, naphthyl and anthracenyl;

aryl-C₁-C₆-alkyl: a straight-chain or branched C₁-C₆-alkyl group asmentioned above, where the alkyl group is substituted by aryl asmentioned above; such as, for example, arylmethyl, 2-arylethyl,1-arylethyl, 3-arylpropyl, 2-arylpropyl;

hetaryl and all hetaryl moieties of correspondingly composed chemicalgroups, such as, for example, hetarylthio, etc.: aromatic mono- orpolycyclic five-or six-membered ring systems which, in addition tocarbon ring members, may also contain 1 to 4 nitrogen atoms or 1 to 3nitrogen atoms and one oxygen or one sulfur atom or one oxygen or onesulfur atom;

imino group —C(R⁴)═NR⁵ is, for example: —HC═NOH, C₁-C₆-alkyl-C═NOH,—HC═NO-C₁-C₆-alkyl, —HC=NO-C₁-C₆-alkylaryl,C₁-C₆-alkyl-C═NO-C₁-C₆-alkyl, —HC═NO-C₂-C₆-alkenyl,C₁-C₆-alkyl-C═NO-C₂-C₆-alkenyl, —HC═N-O-aryl or C₁-C₆-alkyl-C═N-O-aryl.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they are presentas enantiomers or mixtures of diastereomers. The invention provides boththe pure enantiomers or diastereomers and their mixtures. The ratios canvary, depending on the groups. The mixtures can, if appropriate, beseparated by customary methods. The compounds I can be used both as pureisomers and as isomer mixtures.

The compounds of the formula I can also be present in the form of theiragriculturally useful salt, the type of salt usually being immaterial.in general, the salts of those cations or the acid addition salts ofthose acids are suitable whose cations and anions, respectively , do notnegatively affect the herbicidal or fungicidal action of the compoundsI.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, where,if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, di-(2-hydroxyeth -1-yl)ammonium,(2-(2-hydroxyeth-l-oxy)eth-1-yl]-ammonium, diisopropylammonium,tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium,furthermore phosphonium ions, sulfonium ions, preferablytri(C₁-C₄-alkyl)sulfonium and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and also the anions of C₁-C₄-alkanoicacids, preferably formate, acetate, propionate and butyrate.

For the purpose of the present invention, preference is given tocompounds of the formula I having the following structural featuresa.-d., where the compounds may have one or more of the structuralfeatures a.-d.:

a. A is unsubstituted or substituted phenyl or naphthyl.

b. R¹ is unsubstituted or substituted phenyl.

c. R² is hydrogen.

d. R³ is hydrogen; C₁-C₆-alkyl, in particular methyl, ethyl, propyl;C₃-C₇-cycloalkyl, in particular cyclopropyl.

If A or R¹ is phenyl, the phenyl ring may be substituted by one to fiveof the abovementioned radicals, which may be in the 2-, 3- or4-position. Th e phenyl ring is preferably mono- or disubstituted.Preferred substituents are: halogen, alkyl, alkoxy, nitro, cyano,haloalkyl, phenyl.

In the case of monosubstituted phenyl rings, suitable substituents arein particular the following groups: halogen, such as, for example,fluorine, chlorine; alkyl, such as, for example, methyl; alkoxy, suchas, for example, methoxy; nitro; haloalkyl, such as, for example,trifluoromethyl; or cyano. For this purpose, for example the followinggroups are suitable: 4-halophenyl, 4-alkylphenyl, 4-alkoxyphenyl,4-nitrophenyl, 4-cyanophenyl, 4-trifluoromethylphenyl, 2-halophenyl,2-alkylphenyl, 2-alkoxyphenyl, 2-nitrophenyl, 2-cyanophenyl,2-trifluoromethylphenyl, 3-halophenyl, 3-alkylphenyl, 3-alkoxyphenyl,3-nitrophenyl, 3-cyanophenyl, 3-trifluoromethylphenyl.

In the case of disubstituted phenyl rings, suitable substituents are inparticular the following groups, where the substituents may be identicalor different: halogen, such as, for example, chlorine; or alkyl, suchas, for example, methyl. For this purpose, for example the followinggroups are suitable: 2,3-dihalophenyl, 2,4-dihalophenyl,2,5-dihalophenyl, 2,6-dihalophenyl, 3,4-dihalophenyl, 3,5-dihalophenyl,2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl,2,6-dimethylphenyl, 3,4-dimethylphenyl, or 3,5-dimethylphenyl.

A and R¹ are preferably an unsubstituted naphthyl radical or anunsubstituted or substituted phenyl radical, the phenyl radicals beingpreferably mono- or disubstituted by the abovementioned radicals.

For the purpose of the present invention, for example the followingcompounds of Table 1 are suitable:

TABLE 1 Aryl R³ R² R¹ m.p. 1 C₆H₅ H H 2-Cl—C₆H₄ 114 2. C₆H₅ H H3-Cl—C₆H₄ 123 3. C₆H₅ H H 4-Cl—C₆H₄ 151 4. C₆H₅ H H 2,3-Cl₂—C₆H₃ 5. C₆H₅H H 2,4-Cl₂—C₆H₃ 145 6. C₆H₅ H H 2,5-Cl₂—C₆H₃ 7. C₆H₅ H H 2,6-Cl₂—C₆H₃184 8. C₆H₅ H H 3,4-Cl₂—C₆H₃ 9. C₆H₅ H H 3,5-Cl₂—C₆H₃ 166 10. C₆H₅ H H2-CH₃—C₆H₄ 138-139 11. C₆H₅ H H 3-CH₃—C₆H₄ 128 12. C₆H₅ H H 4-CH₃—C₆H₄134 13. C₆H₅ H H 2,3-(CH₃)₂—C₆H₃ 176 14. C₆H₅ H H 2,4-(CH₃)₂—C₆H₃ 13515. C₆H₅ H H 2,5-(CH₃)₂—C₆H₃ 164 16. C₆H₅ H H 2,6-(CH₃)₂—C₆H₃ 179 17.C₆H₅ H H 3,4-(CH₃)₂—C₆H₃ 18. C₆H₅ H H 3,5-(CH₃)₂—C₆H₃ 136 19. C₆H₅ H H4-CH₃O—C₆H₄ 127-129 20. C₆H₅ H H 4-F—C₆H₄ 120-127 21. C₆H₅ H H 4-CN—C₆H₄114-115 22. C₆H₅ H H 4-CF₃—C₆H₄ 149 23. C₆H₅ H H 4-NO₂—C₆H₄ 24. C₆H₅ H H4-C₆H₅—C₆H₄ 25. C₆H₅ H H 2-CH₃O—C₆H₄ 26. C₆H₅ H H 2-F—C₆H₄ 27. C₆H₅ H H2-CN—C₆H₄ 28. C₆H₅ H H 2-CF₃—C₆H₄ 29. C₆H₅ H H 2-NO₂—C₆H₄ 30. C₆H₅ H H2-C₆H₅—C₆H₄ 31. C₆H₅ H H 3-CH₃O—C₆H₄ 32. C₆H₅ H H 3-F—C₆H₄ 33. C₆H₅ H H3-CN—C₆H₄ 34. C₆H₅ H H 3-CF₃—C₆H₄ 35. C₆H₅ H H 3-NO₂—C₆H₄ 36. C₆H₅ H H3-C₆H₅—C₆H₄ 37. C₆H₅ CH₃ H 4-CH₃—C₆H₄ 105-107 38. C₆H₅ CH₃ H 4-Cl—C₆H₄129-131 39. C₆H₅ CH₃ H 4-CH₃O—C₆H₄ 117-118 40. C₆H₅ CH₃ H 4-F—C₆H₄ 41.C₆H₅ CH₃ H 4-CN—C₆H₄ 42. C₆H₅ CH₃ H 4-CF₃—C₆H₄ 43. C₆H₅ CH₃ H 4-NO₂—C₆H₄44. C₆H₅ CH₃ H 4-C₆H₅—C₆H₄ 45. C₆H₅ CH₃ H 2-CH₃—C₆H₄ 46. C₆H₅ CH₃ H2-Cl—C₆H₄ 47. C₆H₅ CH₃ H 2-CH₃O—C₆H₄ 48. C₆H₅ CH₃ H 2-F—C₆H₄ 49. C₆H₅CH₃ H 2-CN—C₆H₄ 50. C₆H₅ CH₃ H 2-CF₃—C₆H₄ 51. C₆H₅ CH₃ H 2-NO₂—C₆H₄ 52.C₆H₅ CH₃ H 2-C₆H₅—C₆H₄ 53. C₆H₅ CH₃ H 3-CH₃—C₆H₄ 54. C₆H₅ CH₃ H3-Cl—C₆H₄ 55. C₆H₅ CH₃ H 3-CH₃O—C₆H₄ 56. C₆H₅ CH₃ H 3-F—C₆H₄ 57. C₆H₅CH₃ H 3-CN—C₆H₄ 58. C₆H₅ CH₃ H 3-CF₃—C₆H₄ 59. C₆H₅ CH₃ H 3-NO₂—C₆H₄ 60.C₆H₅ CH₃ H 3-C₆H₅—C₆H₄ 61. C₆H₅ H H C₆H₅ 62. C₆H₅ CH₃ H C₆H₅ 63. C₆H₅C₂H₅ H 4-Cl—C₆H₄ 64. C₆H₅ C₃H₇ H 4-Cl—C₆H₄ 65. C₆H₅ i.C₃H₇ H 4-Cl—C₆H₄66. C₆H₅ C₄H₉ H 4-Cl—C₆H₄ 67. C₆H₅ c-C₃H₅ H 4-Cl—C₆H₄ 68. 4-Cl—C₆H₄ H HC₆H₅ 69. 4-CH₃—C₆H₄ H H C₆H₅ 70. 4-OCH₃ H H C₆H₅ 71. 4-NO₂—C₆H₄ H H C₆H₅72. 4-CN—C₆H₄ H H C₆H₅ 73. 4-CF₃—C₆H₄ H H C₆H₅ 74. 2-Naphthyl H H C₆H₅75. 3-Naphthyl H H C₆H₅ 76. 4-Cl—C₆H₄ H H 2-Cl—C₆H₄ 77. 4-CH₃—C₆H₄ H H3-Cl—C₆H₄ 78. 4-OCH₃ H H 4-Cl—C₆H₄ 79. 4-NO₂—C₆H₄ H H 2-CH₃—C₆H₄ 80.4-CN—C₆H₄ H H 3-CH₃—C₆H₄ 81. 4-CF₃—C₆H₄ H H 4-CH₃—C₆H₄ 82. 2-Naphthyl HH 3,4-(Cl)₂—C₆H₃ 83. 3-Naphthyl H H 3,4-(Cl)₂—C₆H₃ 84. 4-Cl—C₆H₄ CH₃ HC₆H₅ 85. 4-CH₃—C₆H₄ C₂H₅ H C₆H₅ 86. 4-OCH₃ C₃H₇ H C₆H₅ 87. 4-NO₂—C₆H₄c-C₃H₅ H C₆H₅ 88. 4-CN—C₆H₄ C₄H₉ H C₆H₅ 89. 4-CF₃—C₆H₄ CH₃ H C₆H₅ 90.2-Naphthyl C₂H₅ H C₆H₅ 91. 3-Naphthyl c-C₃H₅ H C₆H₅ 92. 4-Cl—C₆H₄ H HCH₂—CH₂—(CH₃O)₂C₆H₃ 106 93. 3,4-(Cl)₂—C₆H₃ H H C₆H₅ 94. 2,4-(Cl)₂—C₆H₃ HH C₆H₅ 95. 3-Cl—C₆H₄ H H CH₂—CH₂—(CH₃O)₂C₆H₃ oil 96. 4-CH₃—C₆H₄ H HCH₂—CH₂—(CH₃O)₂C₆H₃ 113 97. C₆H₅ H H CH₂—CH₂—(CH₃O)₂C₆H₃ 100 98.2-NO₂—C₆H₄ c-C₃H₅ H C₆H₅ 99. 4-F—C₆H₄ H H CH₂—CH₂—(CH₃O)₂C₆H₃ 100.4-CF₃—C₆H₄ H H CH₂—CH₂—(CH₃O)₂C₆H₃ 101. 2-Naphthyl C₂H₅ H 2-CH₃—C₆H₅102. 3-Naphthyl c-C₃H₅ H 2-Cl—C₆H₅ 103. 3-CH₃—C₆H₄ H HCH₂—CH₂—(CH₃O)₂C₆H₃ 104. 3,4-(Cl)₂—C₆H₃ CH₃ H C₆H₅ 105. 3-Cl—C₆H₄ CH₃ HC₆H₅ 106. 3-CH₃—C₆H₄ C₂H₅ H C₆H₅ 107. 3-OCH₃ C₃H₇ H C₆H₅ 108. 3-NO₂—C₆H₄c-C₃H₅ H C₆H₅ 109. 3-CN—C₆H₄ C₄H₉ H C₆H₅ 110. 3-CF₃—C₆H₄ CH₃ H C₆H₅ 111.4-Cl—C₆H₄ H H 2-Cl—C₆H₄ 121-122 112. 4-Cl—C₆H₄ H H 3-Cl—C₆H₄ 140-141113. 4-Cl—C₆H₄ H H 4-Cl—C₆H₄ 162-163 114. 4-Cl—C₆H₄ H H 2,3-Cl₂—C₆H₃115. 4-Cl—C₆H₄ H H 2,4-Cl₂—C₆H₃ 129-130 116. 4-Cl—C₆H₄ H H 2,5-Cl₂—C₆H₃117. 4-Cl—C₆H₄ H H 2,6-Cl₂—C₆H₃ 213-215 118. 4-Cl—C₆H₄ H H 3,4-Cl₂—C₆H₃119. 4-Cl—C₆H₄ H H 3,5-Cl₂—C₆H₃ 201 120. 4-Cl—C₆H₄ H H 2-CH₃—C₆H₄147-148 121. 4-Cl—C₆H₄ H H 3-CH₃—C₆H₄ 126-127 122. 4-Cl—C₆H₄ H H4-CH₃—C₆H₄ 148-149 123. 4-Cl—C₆H₄ H H 2,3-(CH₃)₂—C₆H₃ 162-163 124.4-Cl—C₆H₄ H H 2,4-(CH₃)₂—C₆H₃ 175 125. 4-Cl—C₆H₄ H H 2,5-(CH₃)₂—C₆H₃ 185126. 4-Cl—C₆H₄ H H 2,6-(CH₃)₂—C₆H₃ 200-201 127. 4-Cl—C₆H₄ H H3,4-(CH₃)₂—C₆H₃ 128. 4-Cl—C₆H₄ H H 3,5-(CH₃)₂—C₆H₃ 190-191 129.4-Cl—C₆H₄ H H 4-CH₃O—C₆H₄ 127-130 130. 4-Cl—C₆H₄ H H 4-F—C₆H₄ 131.4-Cl—C₆H₄ H H 4-CN—C₆H₄ 110 132. 4-Cl—C₆H₄ H H 4-CF₃—C₆H₄ 168 133.4-CH₃—C₆H₄ H H 2-Cl—C₆H₄ 115 134. 4-CH₃—C₆H₄ H H 3-Cl—C₆H₄ 137 135.4-CH₃—C₆H₄ H H 4-Cl—C₆H₄ 113 136. 4-CH₃—C₆H₄ H H 2,3-Cl₂—C₆H₃ 137.4-CH₃—C₆H₄ H H 2,4-Cl₂—C₆H₃ 146 138. 4-CH₃—C₆H₄ H H 2,5-Cl₂—C₆H₃ 139.4-CH₃—C₆H₄ H H 2,6-Cl₂—C₆H₃ 140. 4-CH₃—C₆H₄ H H 3,4-Cl₂—C₆H₃ 141.4-CH₃—C₆H₄ H H 3,5-Cl₂—C₆H₃ 199-201 142. 4-CH₃—C₆H₄ H H 2-CH₃—C₆H₄158-159 143. 4-CH₃—C₆H₄ H H 3-CH₃—C₆H₄ 116-117 144. 4-CH₃—C₆H₄ H H4-CH₃—C₆H₄ 145. 4-CH₃—C₆H₄ H H 2,3-(CH₃)₂—C₆H₃ 146. 4-CH₃—C₆H₄ H H2,4-(CH₃)₂—C₆H₃ 147. 4-CH₃—C₆H₄ H H 2,5-(CH₃)₂—C₆H₃ 148-149 148.4-CH₃—C₆H₄ H H 2,6-(CH₃)₂—C₆H₃ 181-182 149. 4-CH₃—C₆H₄ H H3,4-(CH₃)₂—C₆H₃ 150. 4-CH₃—C₆H₄ H H 3,5-(CH₃)₂—C₆H₃ 157-158 151.4-CH₃—C₆H₄ H H 4-CH₃O—C₆H₄ 152. 4-CH₃—C₆H₄ H H 4-F—C₆H₄ 166-167 153.4-CH₃—C₆H₄ H H 4-CN—C₆H₄ 154. 4-CH₃—C₆H₄ H H 4-CF₃—C₆H₄ 155. C₆H₅ CH₃ H2,4-Cl₂—C₆H₃ oil 156. C₆H₅ CH₃ H 2,4-(CH₃)₂—C₆H₃  82-83 157. C₆H₅ CH₃ H2,4-(CH₃O)₂—C₆H₃ oil 158. C₆H₅ CH₃ H 159. C₆H₅ CH₃ H 160. C₆H₅ i-C₃H₇ H2,4-(CH₃O)₂—C₆H₃ oil 161. C₆H₅ i-C₃H₇ H 2-CH₃—C₆H₄ 102 162. C₆H₅ i-C₃H₇H 4-CH₃—C₆H₄ oil 163. C₆H₅ i-C₃H₇ H 2,4-CH₃—C₆H₃ 118-119 164. C₆H₅i-C₃H₇ H 2-CH₃O—C₆H₄ oil 165. C₆H₅ i-C₃H₇ H 4-CH₃O—C₆H₄ oil 166. C₆H₅i-C₃H₇ H 2-CN—C₆H₄ oil 167. C₆H₅ i-C₃H₇ H 4-CN—C₆H₄ oil 168. C₆H₅ C₂H₅ H2-Cl—C₆H₄ oil 169. C₆H₅ C₂H₅ H 4-Cl—C₆H₄ 106 170. C₆H₅ C₂H₅ H 2-CH₃—C₆H₄oil 171. C₆H₅ C₂H₅ H 4-CH₃—C₆H₄  93-94 172. 4-CH₃—C₆H₄ CH₃ H 2-Cl—C₆H₄oil 173. C₆H₅ C₂H₅ H 2,4-Cl₂—C₆H₃ oil 174. C₆H₅ C₂H₅ H 2,4-(CH₃)₂—C₆H₃oil 175. C₆H₅ C₂H₅ H 2-CH₃O—C₆H₄ oil 176. C₆H₅ C₂H₅ H 4-CH₃O—C₆H₄ oil177. C₆H₅ C₂H₅ H 2,4-(CH₃O)₂—C₆H₃ oil 178. C₆H₅ C₂H₅ H 2-CN—C₆H₄ oil179. C₆H₅ C₂H₅ H 4-CN—C₆H₄ oil 180. 4-CH₃—C₆H₄ CH₃ H 4-Cl—C₆H₄  82 181.4-CH₃—C₆H₄ CH₃ H 2-CH₃—C₆H₄  75-76 182. 4-CH₃—C₆H₄ CH₃ H 4-CH₃—C₆H₄ oil183. 4-CH₃—C₆H₄ CH₃ H 2,4-Cl₂—C₆H₃ 122-124 184. 4-CH₃—C₆H₄ CH₃ H2,4-(CH₃)₂—C₆H₃ 120-121 185. 4-CH₃—C₆H₄ CH₃ H 2-CH₃O—C₆H₄ oil 186.4-CH₃—C₆H₄ CH₃ H 4-CH₃O—C₆H₄ oil 187. 4-CH₃—C₆H₄ CH₃ H 2,4-(CH₃O)₂—C₆H₃oil 188. 4-CH₃—C₆H₄ CH₃ H 2-CN—C₆H₄ 130-132 189. 4-CH₃—C₆H₄ CH₃ H4-CN—C₆H₄ oil 190. C₆H₅ i-C₃H₇ H 2-Cl—C₆H₄ oil 191. 4-Cl—C₆H₄ H H2-CN—C₆H₄ 141-142 192. 4-Cl—C₆H₄ H H 2-OCH₃—C₆H₄ 139 193. 4-Cl—C₆H₄ H H2,4-(CH₃O)₂—C₆H₃ 177 194. 4-CN—C₆H₄ H H 2,4-(CH₃)₂—C₆H₃ 168-169 195.4-CN—C₆H₄ H H 2,4-(Cl)₂—C₆H₃ 189 196. 4-CN—C₆H₄ H H 4-CN—C₆H₃ 187 197.4-CN—C₆H₄ H H 4-Cl—C₆H₃ 204 198. 4-CN—C₆H₄ H H 4-CH₃—C₆H₃ 149 199.4-CN—C₆H₄ H H 4-OCH₃—C₆H₃ 149 200. 4-CN—C₆H₄ H H 2,4-(CH₃O)₂—C₆H₃ 165201. 4-CN—C₆H₄ H H 2-Cl—C₆H₄ 158 202. 4-CN—C₆H₄ H H 2-CH₃—C₆H₄ 164 203.4-CN—C₆H₄ H H 2-OCH₃—C₆H₄  60-66 204. 4-CH₃O—C₆H₄ H H 2-CH₃—C₆H₄ 171-176205. 4-CH₃O—C₆H₄ H H 4-Cl—C₆H₄ 151-155 206. 4-CH₃O—C₆H₄ H H 4-CH₃—C₆H₄130-132 207. 4-CH₃O—C₆H₄ H H 2,4-(CH₃)₂—C₆H₃ 138-140 208. 4-CH₃—C₆H₄i-C₃H₇ H 4-tBu-C₆H₄ 134-136 209. 4-CH₃—C₆H₄ i-C₃H₇ H 4-i-C₃H_(7-C) ₆H₄102-104 210. 4-CH₃—C₆H₄ i-C₃H₇ H 4-F—C₆H₄ oil 211. 4-CH₃—C₆H₄ i-C₃H₇ H2-F—C₆H₄  80-81 212. 4-CH₃—C₆H₄ i-C₃H₇ H 4-CN—C₆H₄  83 213. 4-CH₃—C₆H₄i-C₃H₇ H 2-CN—C₆H₄ oil 214. 4-CH₃—C₆H₄ i-C₃H₇ H 2,4-(CH₃O)₂—C₆H₃ oil215. 4-CH₃—C₆H₄ i-C₃H₇ H 4-OCH₃—C₆H₄ oil 216. 4-CH₃—C₆H₄ i-C₃H₇ H2-OCH₃—C₆H₄  84-85 217. 4-CH₃—C₆H₄ i-C₃H₇ H 2,4-(CH₃)₂—C₆H₃  99 218.4-CH₃—C₆H₄ i-C₃H₇ H 2,4-(Cl)₂—C₆H₃ oil 219. 4-CH₃—C₆H₄ i-C₃H₇ H4-CH₃—C₆H₄  96-97 220. 4-CH₃—C₆H₄ i-C₃H₇ H 2-CH₃—C₆H₄ 133-135 221.4-CH₃—C₆H₄ i-C₃H₇ H 4-Cl—C₆H₄  98-99 222. 4-CH₃—C₆H₄ i-C₃H₇ H 2-Cl—C₆H₄oil 223. 3-Cl—C₆H₄ H H 2-Cl—C₆H₄ 113-114 224. 3-Cl—C₆H₄ H H 4-Cl—C₆H₄122-124 225. 3-Cl—C₆H₄ H H 2-CH₃—C₆H₄ 142-143 226. 3-Cl—C₆H₄ H H4-CH₃—C₆H₄ 114 227. 3-Cl—C₆H₄ H H 2,4-(Cl)₂—C₆H₃ 143 228. 3-Cl—C₆H₄ H H2,4-(CH₃)₂—C₆H₃ 118-119 229. 3-Cl—C₆H₄ H H 2-CH₃O—C₆H₄ 102 230.3-Cl—C₆H₄ H H 4-CH₃O—C₆H₄ 138 231. 3-Cl—C₆H₄ H H 2,4-(CH₃O)₂—C₆H₄118-119 232. 3-CI-C₆H₄ H H 4-CN—C₆H₄  47-55 233. 3-Cl—C₆H₄ H H 2-F—C₆H₄128-131 234. 3-Cl—C₆H₄ H H 4-F—C₆H₄ 132-133 235. 3-Cl—C₆H₄ H H4-i-C₃H_(7-C) ₆H₄ 131-133 236. 3-Cl—C₆H₄ H H 4-t-C₄H_(9-C) ₆H₄ 123-125237. 4-CH₃O—C₆H₄ H H 2,4-(Cl)₂—C₆H₃ 132 238. 4-CH₃O—C₆H₄ H H2,4-(CH₃O)₂—C₆H₃ 115-118 239. 4-CH₃O—C₆H₄ H H 2-CH₃O—C₆H₄ 130 240.4-CH₃O—C₆H₄ H H 2-CN—C₆H₄ 138-139 241. 4-CH₃O—C₆H₄ H H 4-CH₃O—C₆H₄142-143 242. 4-CH₃O—C₆H₄ H H 4-CN—C₆H₄ 128-129 243. 4-CH₃O—C₆H₄ H H2-F—C₆H₄ 132 244. 4-CH₃O—C₆H₄ H H 2-Cl—C₆H₄ 120-121 245. 4-Cl—C₆H₄ H H2-F—C₆H₄ 126-127 246. 4-CN—C₆H₄ H H 2-F—C₆H₄ 146-147 247. 4-Cl—C₆H₄ H H4-i-C₃H₇—C₆H₄ 148-149 248. 4-Ci-C₆H₄ H H 4-t-C₄H₉—C₆H₄ 161-162 249.4-CN—C₆H₄ H H 4-F—C₆H₄ 183-185 250. 4-CN—C₆H₄ H H 4-i-C₃H₇—C₆H₄ 140-149251. 4-CN—C₆H₄ H H 4-t-Bu-C₆H₄  89-93 252. 4-CH₃O—C₆H₄ H H 4-F—C₆H₄127-128 253. 4-CH₃O—C₆H₄ H H 4-i-C₃H₇—C₆H₄ 106-110 254. 4-CH₃—C₆H₄ C₂H₅H 2-Cl—C₆H₄ oil 255. 4-CH₃—C₆H₄ C₂H₅ H 2,4-(Cl)₂—C₆H₃ oil 256.4-CH₃—C₆H₄ C₂H₅ H 2,4-(CH₃)₂—C₆H₃  90-92 257. 4-CH₃—C₆H₄ C₂H₅ H2,4-(CH₃O)₂—C₆H₃ oil 258. 4-CH₃—C₆H₄ C₂H₅ H 4-Cl—C₆H₄  95-96 259.4-CH₃—C₆H₄ C₂H₅ H 2-CH₃—C₆H₄  89-90 260. 4-CH₃—C₆H₄ C₂H₅ H 4-CH₃—C₆H₄ 92-94 261. 4-CH₃—C₆H₄ C₂H₅ H 2-CH₃O—C₆H₄ oil 262. 4-CH₃—C₆H₄ C₂H₅ H4-CH₃O—C₆H₄ oil 263. 4-CH₃—C₆H₄ C₂H₅ H 2-CN—C₆H₄ 133-135 264. 4-CH₃—C₆H₄C₂H₅ H 4-CN—C₆H₄ 135-136 265. 4-CH₃—C₆H₄ C₂H₅ H 2-F—C₆H₄ oil 266.4-CH₃—C₆H₄ C₂H₅ H 4-F—C₆H₄ oil 267. 4-CH₃—C₆H₄ C₂H₅ H 4-i-C₃H₇—C₆H₄ oil268. 4-CH₃—C₆H₄ C₂H₅ H 4-t-Bu-C₆H₄ 105 269. 4-CH₃Ol—C₆H₄ C₂H₅ H4-t-Bu-C₆H₄  65-67 270. 4-Cl—C₆H₄ C₂H₅ H 2-CH₃—C₆H₄  96-97 271.4-Cl—C₆H₄ C₂H₅ H 4-Cl—C₆H₄ 128 272. 4-Cl—C₆H₄ C₂H₅ H 4-CH₃—C₆H₄  87-88273. 4-Cl—C₆H₄ C₂H₅ H 2,4-(Cl)₂—C₆H₃ oil 274. 4-Cl—C₆H₄ C₂H₅ H2,4-(CH₃)₂—C₆H₃ 112 275. 4-Cl—C₆H₄ C₂H₅ H 2-CH₃O—C₆H₄ oil 276. 4-Cl—C₆H₄C₂H₅ H 4-CH₃O—C₆H₄  90-92 277. 4-Cl—C₆H₄ C₂H₅ H 2,4-(CH₃O)₂—C₆H₃ oil278. 4-Cl—C₆H₄ C₂H₅ H 4-CN—C₆H₄ 154 279. 3-CH₃—C₆H₄ H H 2-Cl—C₆H₄  71280. 3-CH₃—C₆H₄ H H 4-Cl—C₆H₄ 117 281. 3-CH₃—C₆H₄ H H 2-CH₃—C₆H₄ 107-109282. 3-CH₃—C₆H₄ H H 4-CH₃—C₆H₄ 112-113 283. 3-CH₃—C₆H₄ H H2,4-(Cl)₂—C₆H₃ 100-102 284. 3-CH₃—C₆H₄ H H 2,4-(CH₃)₂—C₆H₃ 124-126 285.3-CH₃—C₆H₄ H H 2,4-(CH₃O)₂—C₆H₃ 102 286. 3-CH₃—C₆H₄ H H 2-CH₃O—C₆H₄124-125 287. 3-CH₃—C₆H₄ H H 4-CH₃O—C₆H₄ 105-107 288. 3-CH₃—C₆H₄ H H2-CN—C₆H₄  94-98 289. 3-CH₃—C₆H₄ H H 4-CN—C₆H₄  89-90 290. 3-CH₃—C₆H₄ HH 2-F—C₆H₄ 100-101 291. 3-CH₃—C₆H₄ H H 4-F—C₆H₄  91-93 292. 3-CH₃—C₆H₄ HH 4-C₃H₇—C₆H₄  93-94 293. 3-CH₃—C₆H₄ H H 4-t-C₄H₉—C₆H₄  77-79 294.3-CH₃—C₆H₄ H H 3,4-(Cl)₂—C₆H₃ 134-136 295. 3-CH₃—C₆H₄ H H3,4-(CH₃)₂—C₆H₃ 123-125 296. 3-CH₃—C₆H₄ H H 3,4-(F)₂—C₆H₃ 109-110 297.3-CH₃—C₆H₄ H H 3,4-(CH₃O)₂—C₆H₃ oil 298. 3-Cl—C₆H₄ H H 3,4-(F)₂—C₆H₃133-134 299. 3-Cl—C₆H₄ H H 3,4-(CH₃O)₂—C₆H₃ 192-193 300. 3-Cl—C₆H₄ H H3,4-(Cl)₂—C₆H₃ 177 301. 3-Cl—C₆H₄ H H 3,4-(CH₃)₂—C₆H₃  97 302. 4-Cl—C₆H₄H H 3,4-(Cl)₂—C₆H₃ 213-214 303. 4-Cl—C₆H₄ H H 3,4-(CH₃)₂—C₆H₃ 153-154304. 4-Cl—C₆H₄ H H 3,4-(F)₂—C₆H₃ 150-151 305. 4-Cl—C₆H₄ H H3,4-(CH₃O)₂—C₆H₃ 167 306. 4-CN—C₆H₄ H H 3,4-(F)₂—C₆H₃ 178-179 307.4-CN—C₆H₄ H H 3,4-(CH₃)₂—C₆H₃ 144 308. 4-CN—C₆H₄ H H 3,4-(CH₃O)₂—C₆H₃309. 4-CN—C₆H₄ H H 3,4-(Cl)₂—C₆H₃ 260 310. 4-CH₃O—C₆H₄ H H3,4-(Cl)₂—C₆H₃ 162-163 311. 4-CH₃O—C₆H₄ H H 3,4-(CH₃)₂—C₆H₃ 122-123 312.4-CH₃O—C₆H₄ H H 3,4-(F)₂—C₆H₃ 148 313. 4-Cl—C₆H₄ C₂H₅ H 2-Cl—C₆H₄ oil314. 4-Cl—C₆H₄ i-C₃H₇ H 2,4-(Cl)₂—C₆H₃ 113 315. 4-Cl—C₆H₄ i-C₃H₇ H2,4-(CH₃O)₂—C₆H₃ oil 316. 4-Cl—C₆H₄ i-C₃H₇ H 2,4-(CH₃)₂—C₆H₃ 118 317.4-Cl—C₆H₄ i-C₃H₇ H 2-Cl—C₆H₄ oil 318. 4-Cl—C₆H₄ i-C₃H₇ H 3-Cl—C₆H₄110-111 319. 4-Cl—C₆H₄ i-C₃H₇ H 4-Cl—C₆H₄ 126 320. 4-Cl—C₆H₄ i-C₃H₇ H2-CH₃—C₆H₄ 138 321. 4-Cl—C₆H₄ i-C₃H₇ H 4-CH₃—C₆H₄  95-96 322. 4-Cl—C₆H₄i-C₃H₇ H 4-CN—C₆H₄ 167-168 323. 4-Cl—C₆H₄ i-C₃H₇ H 2-CN—C₆H₄ 109 324.4-Cl—C₆H₄ i-C₃H₇ H 4-CH₃O—C₆H₄ oil 325. 3-CF₃—C₆H₄ H H 2-Cl—C₆H₄  93-95326. 3-CF₃—C₆H₄ H H 4-Cl—C₆H₄ 166-167 327. 3-CF₃—C₆H₄ H H 2-CH₃—C₆H₄141-142 328. 3-CF₃—C₆H₄ H H 4-CH₃—C₆H₄ 144-146 329. 3-CF₃—C₆H₄ H H2-CH₃O—C₆H₄ oil 330. 3-CF₃—C₆H₄ H H 4-CH₃O—6H₄ 138 331. 3-CF₃—C₆H₄ H H4-CN—C₆H₄ 122 332. 3-CF₃—C₆H₄ H H 2-F—C₆H₄  85-86 333. 3-CF₃—C₆H₄ H H4-F—C₆H₄ 133-134 334. 3-CF₃—C₆H₄ H H 4-i-C₃H₇—C₆H₄ 127-128 335.3-CF₃—C₆H₄ H H 4-t-C₄H₉—C₆H₄ 133-134 336. 3-CF₃—C₆H₄ H H 3,4-(Cl)₂—C₆H₃178-179 337. 3-CF₃—C₆H₄ H H 3,4-(CH₃)₂—C₆H₃ 116 338. 3-CF₃—C₆H₄ H H3,4-(F)₂—C₆H₃ 110 339. 3-CF₃—C₆H₄ H H 2,4-(CH₃)₂—C₆H₃  95-96 340.3-CF₃—C₆H₄ H H 2,4-(Cl)₂—C₆H₃ 120 341. 3-CF₃—C₆H₄ H H 3,4-(CH₃O)₂—C₆H₃144 342. 3-CF₃—C₆H₄ H H 2,4-(CH₃O)₂—C₆H₃ 125 343. 3,5-(Cl)₂C₆H₃ H H2-Cl—C₆H₄ 160 344. 3,5-(Cl)₂C₆H₃ H H 4-Cl—C₆H₄ 214 345. 3,5-(Cl)₂C₆H₃ HH 2-CH₃—C₆H₄ 180-182 346. 3,5-(Cl)₂C₆H₃ H H 4-CH₃—C₆H₄ 166 347.3,5-(Cl)₂C₆H₃ H H 2-CH₃O—C₆H₄ 164 348. 3,5-(Cl)₂C₆H₃ H H 4-CH₃O—C₆H₄ 181349. 3,5-(Cl)₂C₆H₃ H H 2-F—C₆H₄ 169 350. 3,5-(Cl)₂C₆H₃ H H 4-CN—C₆H₄ 160351. 3,5-(Cl)₂C₆H₃ H H 4-F—C₆H₄ 164 352. 3,5-(Cl)₂C₆H₃ H H 4-i-C₃H₇—C₆H₄oil 353. 3,5-(Cl)₂C₆H₃ H H 4-t-C₄H₉—C₆H₄ 158-160 354. 3,5-(Cl)₂C₆H₃ H H2,4-(Cl)₂—C₆H₃ 153-155 355. 3,5-(Cl)₂C₆H₃ H H 2,4-(CH₃)₂—C₆H₃ 205 356.3,5-(Cl)₂C₆H₃ H H 2,4-(CH₃O)₂—C₆H₃ 175 357. 3,5-(Cl)₂C₆H₃ H H3,4-(Cl)₂—C₆H₃ 226-229 358. 3,5-(Cl)₂C₆H₃ H H 3,4-(CH₃)₂—C₆H₃ 145 359.3,5-(Cl)₂C₆H₃ H H 3,4-(F)₂—C₆H₃ oil 360. 3,5-(Cl)₂C₆H₃ H H3,4-(CH₃O)₂—C₆H₃ oil

The compounds of the formula I can be prepared analogously to theprocess as described in the literature (cf. DD 156663, J.Am.Chem.Soc. 39(1908), 63). The synthesis is carried out, for example, by the followingstandard process, where the phenyl rings in formula II or III may beunsubstituted or substituted:

X is a suitable leaving group, such as, for example, halogen or alkoxy.

The cyanocarboxylic acid derivatives of the formula II can be preparedby processes known from the literature (cf. Org. Synthesis, Collect VolIV, 1963, p. 461 ff.). The phenylamines of the formula III are eithercommercially available, or they can also be prepared by processes knownfrom the literature.

The compounds of the formula I are suitable for use as active compoundsfor preparing crop protection compositions. For the purpose of thepresent invention, crop protection compositions are generally understoodas being mixtures of active compounds of the formula I with additives orauxiliaries which make possible the use of the mixtures in agricultureor gardening and the application of these compositions onto areas freefrom crops or for treating plants. The crop protection compositions canpreferably be employed as herbicides and/or fungicides.

The plants are usually sprayed or dusted with the active compounds orthe crop protection compositions, or the seeds of the plants are treatedwith the active compounds.

The compounds of the formula I and their agriculturally useful salts aresuitable, both in the form of stereoisomeric mixtures and in the form ofthe pure stereoisomers, especially as herbicides. The herbicidalcompositions comprising the compounds of the formula I control plantgrowth on non-crop areas very efficiently, especially at high rates ofapplication. They act against broad-leaved weeds and grass weeds incrops such as wheat, rice, maize, soybean and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Depending on the particular application method, the compounds of theformula I or the compositions comprising them can additionally beemployed in a further number of crop plants for eliminating undesirableplants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum,(Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

In addition, the compounds of the formula I can also be used in cropswhich tolerate the action of herbicides owing to breeding, includinggenetic engineering methods.

The compounds of the formula I or the compositions comprising them canbe used, for example, in the form of ready-to-spray aqueous solutions,powders, suspensions, also highly-concentrated aqueous, oily or othersuspensions or dispersions, emulsions, oil dispersions, pastes, dusts,materials for broadcasting, or granules, by means of spraying,atomizing, dusting, broadcasting or watering. The use forms depend onthe intended aims; in any case, they should ensure the finest possibledistribution of the active compounds according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I and auxiliaries which are customary for formulating crop protectionagents.

Suitable inert auxiliaries are essentially: mineral oil fractions ofmedium to high boiling point, such as kerosene and diesel oil,furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, for example paraffins,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols, such as methanol,ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone,or strongly polar solvents, for example amines such asN-methylpyrrolidone, or water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thecompounds of the formula I, either as such or dissolved in an oil orsolvent, can be homogenized in water by means of a wetting agent,tackifier, dispersant or emulsifier. Alternatively, it is possible toprepare concentrates comprising active compound, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil,which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, for example ligno-,phenol-, naphthalene- and dibutylnapthalenesulfonic acid, and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesor sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene, or of the naphthalene sulfonic acids withphenol and formaldehyde, polyoxyethylene octyl phenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenol or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ether or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite wasteliquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor jointly grinding the active substances together with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active compounds tosolid carriers. Solid carriers are mineral earth, such as silicas,silica gels, silicates, talc, kaolin, limestone, lime, chalk, bowl,loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesiumsulfate, magnesium oxide, ground synthetic materials, fertilizers, suchas ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight of at least one active compound. The active compounds areemployed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The compounds I according to the invention can be formulated, forexample, as follows:

a) 20 parts by weight of a compound I are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acidN-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonateand 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 molof castor oil. Pouring the solution into 100 000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersionwhich comprises 0.02% by weight of the active compound.

b) 20 parts by weight of a compound I are dissolved in a mixturecomposed of 40 parts by weight of cyclohexanone, 30 parts by weight isisobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxideto 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into100 000 parts by weight of water and finely distributing it thereingives an aqueous dispersion which comprises 0.02% by weight of theactive compound.

c) 20 parts by weight of a compound I are dissolved in a mixturecomposed of 25 parts by weight of cyclohexanone, 65 parts by weight of amineral oil fraction of boiling point 210 to 2800C and 10 parts byweight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.Pouring the solution into 100 000 parts by weight of water and finelydistributing it therein gives an aqueous dispersion which comprises0.02% by weight of the active compound.

d) 20 parts by weight of a compound I are mixed thoroughly with 3 partsby weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weightof the sodium salt of a lignosulfonic acid from a sulfite waste liquorand 60 parts by weight of pulverulent silica gel, and the mixture isground in a hammer mill. Finely distributing the mixture in 20000 partsby weight of water gives a spray mixture which comprises 0.1% by weightof the active compound.

e) 3 parts by weight of a compound I are mixed with 97 parts by weightof finely divided kaolin. This gives a dust which comprises 3% by weightof active compound.

f) 20 parts by weight of a compound I are mixed intimately with 2 partsby weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fattyalcohol polyglycol ether, 2 parts by weight of the sodium salt of aphenol/urea/formaldehyde condensate and 68 parts by weight of aparaffinic mineral oil. This gives a stable oily dispersion.

g) 1 part by weight of a compound I is dissolved in a mixture composedof 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. This gives a stable emulsion concentrate.

h) 1 part by weight of a compound I is dissolved in a mixture composedof 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol®EM 31 (nonionic emulsifier based on ethoxylated castor oil). This givesa stable emulsion concentrate.

The active compounds of the formula I or the herbicidal compositions canbe applied pre- or post-emergence. If the active compounds are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that they come into as little contactas possible, if any, with the leaves of the sensitive crop plants, whilethe active compounds reach the leaves of undesirable plants growingunderneath, or the bare soil surface (post-directed, lay-by).

To widen the spectrum of action and to achieve synergistic effects, thecompounds of the formula I may be mixed with a large number ofrepresentatives of other herbicidal or growth-regulating groups ofactive compounds and then applied concomitantly. Suitable components formixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles,amides, aminophosphoric acid and its derivatives, aminotriazoles,anilides, aryloxy/hetaryloxyalkanoic acid and its derivatives, benzoicacid and its derivatives, benzothiadiazinones,2-(aroyl/hetaroyl)-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinoline carboxylic acid and its derivatives, chloroacetanilides,cyclohexenenone oxime ether derivatives, diazines, dichloropropionicacid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- andheteroaryloxyphenoxypropionic esters, phenyl acetic acid and itsderivatives, phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonyl ureas, triazines,triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formulaI, alone or in combination with other herbicides, in the form of amixture with other crop protection agents, for example together withagents for controlling pests of phytopathogenic fungi or bacteria. Alsoof interest is the miscibility with mineral salt solutions, which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates may also be added.

Depending on the control target, the season, the target plant and thegrowth stage, the active compound application rates are from 0.001 to3.0, preferably from 0.01 to 1.0, kg of active substance (a. S.)/ha.

Compounds of the formula I also have fungicidal action. They aredistinguished, in particular, by excellent action against a broadspectrum of phytopathogenic fungi, especially from the classes of theAscomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some ofthem act systemically, and they can therefore also be employed as folia-and soil-acting fungicides.

They are of particular importance for controlling a large number offungi in various crop plants, such as wheat, rye, barley, oats, rice,maize, turf, cotton, soybean, coffee, sugarcane, grapevines, fruits andornamental plants and vegetables, such as cucumbers, beans andcucurbits, and in the seeds of these plants.

The compounds are applied by treating the fungi or the seeds, plants,materials or the soil to be protected against fungal attack with afungicidally active amount of the active compounds. Application iscarried out before or after the infection of the materials, plants orseeds by the fungi.

The novel compounds are particularly suitable for controlling thefollowing plant diseases: Erysiphe graminis (powdery mildew) in cereals,Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,Podosphaera leucotricha in apples, Uncinula necator in grapevines,Puccinia species in cereals, Rhizoctonia species in cotton and turf,Ustilago species in cereals and sugarcane, Venturia inaequalis (scab) inapples, Helminthosporium species in cereals, Septoria nodorum in wheat,Botrytis cinerea (gray mold) in strawberries, grapevines, ornamentalplants and vegetables, Cercospora arachidicola in groundnuts,Pseudocercosporella herpotrichoides in wheat, barley, Pyricularia oryzaein rice, Phytophthora infestans in potatoes and tomatoes, Fusarium andVerticillium species in a variety of plants, Plasmopara viticola ingrapevines, Alternaria species in vegetables and fruit.

The active compounds of the formula I can also be employed in theprotection of materials (wood protection), for example againstPaecilomyces variotii.

The fungicidal compositions generally comprise between 0.1 and 95,preferably between 0.5 and 90, % by weight of active compound.

Depending on the nature of the desired effect, the application rates arebetween 0.025 and 2, preferably from 0.1 to 1, kg of active compound perha.

In the treatment of seed, amounts of active compound of generally from0.001 to 50, preferably from 0.01 to 10, g per kilogram of seed arerequired.

In the use form as fungicides, the compositions according to theinvention can also be present together with other active compounds, forexample with herbicides, insecticides, growth regulators, fungicides orelse with fertilizers.

When the compounds are mixed with fungicides, in many cases this resultsin a broadening of the fungicidal activity spectrum.

The following list of fungicides which can be applied jointly with thecompounds according to the invention is meant to illustrate the possiblecombinations, without imposing a limitation: fungicides from the activecompound group of the sulfur compounds, dithibcarbamates and theirderivatives; nitro derivatives; heterocyclic substances, such as, forexample, imidazoline derivatives, triazoles, triazine derivatives,quinoxaline derivatives, benzimidazole derivatives, thiadiazolederivatives, etc.; or strobilurins.

The following working examples illustrate the invention in more detail:

EXAMPLE 1

N-(3-chlorophenyl)-2-cyano-2-phenylacetamide (Compound No. 2 fromTable 1) 3 g (0.016 mol) of ethyl phenylcyanoacetate and 2 g (0.016 mol)of 3-chloroaniline are heated undiluted at 130° C. for 5 hours. Themixture is subsequently taken up in 100 ml of dichloromethane andextracted three times with 10% strength hydrochloric acid. The organicphase is separated off, dried and concentrated. The resulting residue istaken up in 30 ml of dichloromethane, and 200 ml of petroleum ether areadded. The resulting crystalline precipitate is filtered off withsuction, washed with petroleum ether and dried. Yield 38%; m.p. 123° C.

EXAMPLE 2

Herbicidal Action

The herbicidal action of the compounds according to the invention isinvestigated using the representative test model below. The effect ofthe test substances on the growth of duck weed is determined by thefollowing method:

The duct weed Lemna paucicostata was grown under sterile conditions and250 ml glass vessels containing 100 ml of inorganic nutrient solutionand supplemented with 1% sucrose, as described by Grossmann et al.,Pesticide Science 35, (1992), 283-289. At the beginning of the test, 150μl of a solution of active compound in acetone (stock solution: 100-foldconcentrated) were pipetted into Petri dishes (diameter 6 cm, height 1.5cm; Greiner, Frickenhausen) containing 15 ml of nutrient solution.(without added sucrose). Only the solvent component of the activecompound solution was added to the nutrient solution for the controltests. Then, 4 Lemna plants were introduced into each dish, the disheswere covered with lids and incubated under permanent light conditions at25° C. After 8-10 days, the increase in leaf area was determined usingan imaging apparatus (Imago, Compulog Computer Syst., Böblingen) asgrowth parameter, and this was used to calculate the growth inhibitionas a percentage relative to the control.

The results of the tests can be seen from the table which follows. Theherbicidal effect of the compounds according to the invention isdemonstrated by the potent inhibition of the growth of Lemna.

Growth inhibition Concentration (% relative to the Compound (μmolar)control) A 100 100 10 93 1 40 A = N-(3,4-dichlorophenyl)-2-cyano-2-phenylacetamide

(Table 1, Comp. No. 8)

EXAMPLE 3

Fungicidal Action

Activity against Pyricularia oryzae (protective)

Leaves of potted rice seedlings c.v. “Tai-Nong 67” were sprayed to runoff point with an aqueous preparation of active compound which had beenprepared from a stock solution comprising 10% of active compound, 63% ofcyclohexanone and 27% of emulsifier. The following day, the plants wereinoculated with an aqueous spore suspension of Pyricularia oryzae. Thetest plants were subsequently placed in controlled-environment chambersat 22-24° C. and 95-99% relative atmospheric humidity for 6 days. Theextent of the development of the infection on the leaves was thendetermined visually.

% infection of the leaves after applica- Active compound tion of anaqueous preparation contain- from Table 1 ing 250 ppm of active compoundNo. 5 15 No. 7 7 No. 14 15 No. 15 5 Control 85 (untreated)

EXAMPLE 4

Fungicidal Action

Activity Against Plasmopara viticola

Leaves of potted grapevines c.v. “Müller-Thurgau” were sprayed to runoff point with an aqueous preparation of active compound which had beenprepared using a stock solution comprising 10% of active compound, 63%of cyclohexanone and 27% of emulsifier. In order to be able to assessthe persistency of the substances, the plants were kept for 7 days in agreenhouse after the spray coating had dried on. Only then were theleaves inoculated with an aqueous zoospore suspension of Plasmoparaviticola. The grapevines were then initially kept in a watervapor-saturated chamber at 24° C. for 48 hours and then in a greenhouseat 20 and 30° C. for 5 days. After this period of time, the plants wereonce more kept in a humid chamber for 16 hours to promote sporangiophoreeruption. The extent of the infection on the undersides of the leaveswas then determined visually.

% infection of the leaves after applica- Active compound tion of anaqueous preparation contai- from Table 1 ning 250 ppm of active compoundNo. 2 0 No. 14 0 No. 18 10 Control 90 (untreated)

We claim:
 1. A method for controlling harmful fungi; or for controlling undesirable growth of harmful plants, which comprises bringing i) the fungi, their habitat or materials, plants, seeds, soils, areas or spaces to be protected against fungal attack, and/or ii) the harmful plants or their habitat into contact with an effective amount of at least one compound of the formula I

where the radicals have the following meanings: A is aryl which can be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₃-C₆-alkynyl-C₁-C₆-alkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkyl-C₃-C₇-cycloalkyl, C₁-C₆-alkoxy-C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₃-C₇-cyanocycloalkoxy, C₁-C₆-alkyl-C₃-C₇-cycloalkoxy, C₃-C₇-halocycloalkyl, C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy, C₅-C₇-cycloalkenyl, C₁-C₆-alkyl-C₅-C₇-cycloalkenyl, C₁-C₆-alkoxy-C₅-C₇-cycloalkenyl, C₅-C₇-cyano-cycloalkenyl, C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl, C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy, C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-cyanoalkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarboxyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino, arylcarbonylamino, arylsulfinyl, arylsufonyl, heteroarylsulfinyl, heteroarylsulfonyl, aryl-C₁-C₆-alkyl, aryl-C₂-C₆-alkenyl, aryl-C₃-C₆-alkynyl, aryl-C₁-C₆-alkoxy, aryl-C₂-C₆-alkenyloxy, aryl-C₃-C₆-alkynyloxy, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, aryl, aryloxy, arylthio or —C(R⁴)═NR⁵, R¹ is aryl or aryl-C₁-C₆-alkyl, where the aryl radical can in each case be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆alkenyl -C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₃-C₆-alkynyl-C₁-C₆-alkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkyl-C₃-C₇-cycloalkyl, C₁-C₆-alkoxy-C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₃-C₇-cyanocycloalkoxy, C₁-C₆-alkyl-C₃-C₇-cycloalkoxy, C₃-C₇-halocycloalkyl, C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy, C₅-C₇-cycloalkenyl, C₁-C₆-alkyl-C₅-C₇-cycloalkenyl, C₁-C₆-alkoxy-C₅-C₇-cycloalkenyl, C₅-C₇-cyanocycloalkenyl, C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl, C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy, C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-cyanoalkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarboxyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-C₁-C₆-alkyl, aryl-C₂-C₆-alkenyl, aryl-C₃-C₆-alkynyl, aryl-C₁-C₆-alkoxy, aryl-C₂-C₆-alkenyloxy, aryl-C₃-C₆-alkynyloxy, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, aryl, aryloxy, arylthio or —C(R⁴)═NR⁵, R², R³ are hydrogen, C₁-C₆-alky, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylaryl, which may be unsubstituted or partially or fully halogenated or may carry one to three substituents selected from the group consisting of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₃-C₇-cycloalkyl, C₅-C₇-cycloalkenyl; R⁴ is hydrogen or C₁-C₆-alkyl, R⁵ is hydroxyl, C₁-C₄-alkoxy, aryl-C₁-C₄-alkoxy, aryloxy, or an agriculturally useful salt thereof or a composition comprising at least one of these compounds.
 2. The method as claimed in claim 1, where A is not unsubstituted phenyl if R³ is hydrogen or C₁-C₅-alkyl and R¹ is aryl, halogen-substituted aryl or arlyalkyl.
 3. The method as claimed in claim 1, where A is unsubstituted or substituted phenyl or naphthyl.
 4. The method as claimed in claim 1, where R¹ is unsubstituted or substituted phenyl.
 5. The method as claimed in claim 1, where R² is hydrogen.
 6. The method as claimed in claim 1, where R³ is hydrogen; C₁-C₆-alkyl or C₃-C₇-cycloalkyl.
 7. The method as claimed in claim 1, where A or R¹ is substituted phenyl, the phenyl ring being mono-, di- or trisubstituted by halogen, alkyl, alkoxy, nitro, cyano, haloalkyl or phenyl.
 8. The method as claimed in claim 7, where the phenyl ring is monosubstituted by halogen, alkyl, alkoxy, nitro, haloalkyl or cyano.
 9. The method as claimed in claim 8, where the phenyl ring has the following meanings: 4-halophenyl, 4-alkylphenyl, 4-alkoxyphenyl, 4-nitrophenyl, 4-cyanophenyl, 4-trifluoromethylphenyl, 2-halophenyl, 2-alkylphenyl, 2-alkoxyphenyl, 2-nitrophenyl, 2-cyanophenyl, 2-trifluoromethylphenyl, 3-halophenyl 3-alkylphenyl, 3-alkoxyphenyl, 3-nitrophenyl, 3-cyanophenyl, 3-trifluoromethylphenyl.
 10. The method as claimed in claim 7, where the phenyl ring is disubstituted by halogen or alkyl.
 11. The method as claimed in claim 10, where the phenyl ring has the following meanings: 2,3-dihalophenyl; 2,4-dihalophenyl; 2,5-dihalophenyl; 2,6-dihalophenyl; 3,4-dihalophenyl; 3,5-dihalo- phenyl; 2,3-dimethylphenyl; 2,4-dimethylphenyl; 2,5-dimethyl- phenyl; 2,6-dimethylphenyl; 3,4-dimethylphenyl or 3,5-dimethylphenyl.
 12. A compound selected from: N-(3-chlorphenyl)-2-cyano-2-phenylacetamide; N-(2,5-dichlorphenyl)-2-cyano-2-phenylacetamide; N-(2,6-dichlorphenyl)-2-cyano-2-phenylacetamide; N-(3,5-dichlorphenyl)-2-cyano-2-phenylacetamide; N-(3-chlorphenyl)-2-cyano-2-phenylpropamide; N-(4-fluorphenyl)-2-cyano-2-phenylacetamide; N-(2-fluorphenyl)-2-cyano-2-phenylacetamide; N-(3-fluorphenyl)-2-cyano-2-phenylacetamide; N-(4-fluorphenyl)-2-cyano-2-phenylpropamide; N-(2-fluorphenyl)-2-cyano-2-phenylpropamide; N-(3-fluorphenyl)-2-cyano-2-phenylpropamide.
 13. The method of claim 6, wherein R³ is hydrogen, methyl, ethyl, propyl or cyclopropyl.
 14. A crop protection composition comprising at least one compound of formula I

wherein A is aryl which can be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, mitre, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₃-C₆-alkynyl-C₁-C₆-alkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkyl-C₃-C₇-cycloalkyl, C₁-C₆-alkoxy-C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₃-C₇-cyanocycloalkoxy, C₁-C₆-alkyl-C₃-C₇-cycloalkoxy, C₃-C₇-halocycloalkyl, C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy, C₅-C₇-cycloalkenyl, C₁-C₆-alkyl-C₅-C₇-cycloalkenyl, C₁-C₆-alkoxy-C₅-C₇-cycloalkenyl, C₅-C₇-cyanocycloalkenyl, C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl, C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy, C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-cyanoalkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkyl-carboxyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino, arylcarbonylamino, arylsulfinyl, arylsufonyl, heteroarylsulfinyl, heteroarylsulfonyl, aryl-C₁-C₆-alkyl, aryl-C₂-C₆-alkenyl, aryl-C₃-C₆-alkynyl, aryl-C₂-C₆-alkoxy, aryl-C₂-C₆-alkenyloxy, aryl-C₃-C₆-alkynyloxy, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, aryl, aryloxy, arylthio or —C(R⁴)═NR⁵, R¹ is aryl or aryl-C₁-C₆-alkyl, where the aryl radical can in each case be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₃-C₆-alkynyl-C₁-C₆-alkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkyl-C₃-C₇-cycloalkyl, C₁-C₆-alkoxy-C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₃-C₇-cyanocycloalkoxy, C₁-C₆-alkyl-C₃-C₇-cycloalkoxy, C₃-C₇-halocycloalkyl, C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy, C₅-C₇-cycloalkenyl, C₁-C₆-alkyl-C₅-C₇-cycloalkenyl, C₁-C₆-alkoxy-C₅-C₇-cycloalkenyl, C₅-C₇-cyanocycloalkenyl, C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl, C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy, C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-alkylthio, C₁-C₆-cyanoalkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarboxyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-C₁-C₆-alkyl, aryl-C₂-C₆-alkenyl, aryl-C₃-C₆-alkynyl, aryl-C₁-C₆-alkoxy, aryl-C₂-C₆-alkenyloxy, aryl-C₃-C₆-alkynyloxy, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, aryl, aryloxy, arylthio or —C(R⁴)═NR⁵, R², R³ are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylaryl, which may be unsubstituted or partially or fully halogenated or may carry one to three substituents selected from the group consisting of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₃-C₇-cycloalkyl, C₅-C₇-cycloalkenyl; R⁴ is hydrogen or C₄-C₆-alkyl, R⁵ is hydroxyl, C₁-C₄-alkoxy, aryl-C₁-C₄-alkoxy, aryloxy, with the proviso that if A is an unsubstituted phenyl group and R³ is hydrogen or alkyl, R¹ is not aryl, arylalkyl or halogen-substituted aryl, and the proviso that if R³ is hydrogen, A is not 2-nitrophenyl or 2-aminophenyl.
 15. A compound of formula I

wherein A is aryl which can be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, mitre, hydroxyl, mercapto, thiocyanato, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₃-C₆-alkynyl-C₁-C₆-alkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkyl-C₃-C₇-cycloalkyl, C₁-C₆-alkoxy-C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₃-C₇-cyanocycloalkoxy, C₁-C₆-alkyl-C₃-C₇-cycloalkoxy, C₃-C₇-halocycloalkyl, C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy, C₅-C₇-cycloalkenyl, C₁-C₆-alkyl-C₅-C₇-cycloalkenyl, C₁-C₆-alkoxy-C₅-C₇-cycloalkenyl, C₅-C₇-cyanocycloalkenyl, C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl, C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy, C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-cyanoalkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarboxyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino, heteroarylsulfinyl, heteroarylsulphonyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, or —C(R⁴)═NR⁵, R¹ is aryl or aryl-C₁-C₆-alkyl, where the aryl radical can in each case be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₃-C₆-alkynyl-C₁-C₆-alkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkyl-C₃-C₇-cycloalkyl, C₁-C₆-alkoxy-C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₃-C₇-cyanocycloalkoxy, C₁-C₆-alkyl-C₃-C₇-cycloalkoxy, C₃-C₇-halocycloalkyl, C₃-C₇-cyanocycloalkyl, C₃-C₇-halocycloalkoxy, C₅-C₇-cycloalkenyl, C₁-C₆-alkyl-C₅-C₇-cycloalkenyl, C₁-C₆-alkoxy-C₅-C₇-cycloalkenyl, C₅-C₇-cyanocycloalkenyl, C₅-C₇-halocycloalkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-haloalkynyl, C₂-C₆-cyanoalkenyl, C₃-C₆-cyanoalkynyl, C₁-C₆-alkoxy, C₁-C₆-cyanoalkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-cyanoalkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-cyanoalkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarboxyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-C₁-C₆-alkyl, aryl-C₂-C₆-alkenyl, aryl-C₃-C₆-alkynyl, aryl-C₁-C₆-alkoxy, aryl-C₂-C₆-alkenyloxy, aryl-C₃-C₆-alkynyloxy, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, aryl, aryloxy, arylthio or —C(R⁴)═NR⁵, R², R³ are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylaryl, which may be unsubstituted or partially or fully halogenated or may carry one to three substituents selected from the group consisting of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₃-C₇-cycloalkyl, C₅-C₇-cycloalkenyl; R⁴ is hydrogen or C₄-C₆-alkyl, R⁵ is hydroxyl, C₁-C₄-alkoxy, or a salt thereof, except for the compounds wherein (a) A is unsubstituted phenyl, R³ is hydrogen or alkyl, and R¹ is unsubstituted phenyl or halogen-substituted phenyl, (b) A is unsubstituted phenyl, R³ is hydrogen or C₁-C₅-alkyl, and R¹ is aryl, halogen-substituted aryl or arylakyl, (c) R¹ is phenyl, naphtyl or phenyl-C₁-C₄-alkyl, R² is hydrogen, alkyl, alkenyl or C₅-C₇-cycloalkyl, and R³ is hydrogen, and (d) A is 2-nitrophenyl or 2-aminophenyl and R³ is hydrogen; and except for the following compounds: N-(4-ethoxyphenyl)-2-cyano-2-phenyl hexamide; N-(4-ethoxyphenyl)-2-cyano-2-phenylbutamide; N-(2,4,6-trimethoxyphenyl)-2-cyano-2-phenylacetamide; N-(2,6-dimethylphenyl)-2-cyano-2-(4-methoxyphenyl)acetamide; N-(2-methylphenyl)-2-cyano-2-phenylacetamide; N-(3-methylphenyl)-2-cyano-2-phenylacetamide; N-(4-methylphenyl)-2-cyano-2-phenylacetamide.
 16. The compound defined in claim 15, wherein A is unsubstituted or substituted phenyl or naphthyl.
 17. The compound defined in claim 15, wherein R¹ is unsubstituted or substituted phenyl.
 18. The compound defined in claim 15, wherein R² is hydrogen.
 19. The compound defined in claim 15, wherein R³ is hydrogen, C₁-C₆-alkyl or C₃-C₇-cycloalkyl.
 20. The compound defined in claim 15, wherein R³ is hydrogen, methyl, ethyl, propyl or cyclopropyl.
 21. The compound defined in claim 15, wherein if A is substituted phenyl, the phenyl ring is mono-, di- or trisubstituted by halogen, alkyl, alkoxy, cyano, haloalkyl or phenyl, and if R¹ is substituted phenyl, the phenyl ring is mono-, di- or trisubstituted by halogen, alkyl, alkoxy, nitro, cyano, haloakyl or phenyl.
 22. The compound defined in claim 21, wherein the phenyl ring in position A is monosubstituted by ahlogen, alkyl, alkoxy, haloalkyl or cyano; and the phenyl ring in position R¹ is monosubstituted by halogen, alkyl, alkoxy, nitro, haloalkyl or cyano.
 23. The compound defined as claim 22, wherein A has the following meanings: 4-halophenyl, 4-alkylphenyl, 4-alkoxyphenyl, 4-cyanophenyl, 4-trifluoromethylphenyl, 2-halophenyl, 2-alkylphenyl, 2-alkoxyphenyl, 2-cyanophenyl, 2-trifluoromethylphenyl, 3-halophenyl, 3-alkylphenyl, 3-alkoxyphenyl, 3-cyanophenyl or 3-trifluoromethylphenyl, and R¹ has the following meanings: 4-halophenyl, 4-alkylphenyl, 4-alkoxyphenyl, 4-nitrophenyl, 4-cyanophenyl, 4-trifluoromethylphenyl, 2-halophenyl, 2-alkylphenyl, 2-alkoxyphenyl, 2-nitrophenyl, 2-cyanophenyl, 2-trifluoromethylphenyl, 3-halophenyl, 3-alkylphenyl, 3-alkoxyphenyl, 3-nitrophenyl, 3-cyanophenyl or 3-trifluoromethylphenyl.
 24. The compound defined in claim 21, wherein the phenyl ring in position A or R¹ is disubstituted by halogen or alkyl.
 25. The compound defined in claim 24, wherein the phenyl ring in position A or R¹ has the following meanings: 2,3-dihalophenyl; 2,4-dihalophenyl; 2,5-dihalophenyl; 2,6-dihalophenyl; 3,4-dihalophenyl; 3,5-dihalophenyl; 2,3-dimethylphenyl; 2,4-dimethylphenyl; 2,5-dimethylphenyl; 2,6-dimethylphenyl; 3,4-dimethylphenyl or 3,5-dimethylphenyl. 